Abstract
The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1H-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a quantitative yield. The kinetics of a conjugate addition of pyrrole was studied in detail to reveal the substituent effect and activation parameters of the reaction. The subsequent base-induced elimination of nitrous acid afforded a series of novel 2-(2-Fluoro-1-arylvinyl)-1H-pyrroles prepared in up to an 85% isolated yield. The two-step sequence herein proposed is an indispensable alternative to a direct reaction with elusive and unstable 1-Fluoroacetylenes.
Highlights
The conjugate addition of 2-unsubstituted pyrroles to Michael acceptors is a powerful tool used for their further functionalization [9,10,11,12]
We report a yielding catalyst-free conjugate addition of pyrroles to pyrroles to β-Fluoro-β-nitrostyrenes, novel
A family of novel adducts was synthesized in a quantitative yield
Summary
Pyrrole and its derivatives are widely used as intermediates in the synthesis of pharmaceuticals, agrochemicals, dyes and other valuable organic compounds [2,3,4,5]. Many drugs containing a pyrrole moiety are available in the market or are currently undergoing clinical trials [6]. They exhibit a wide range of biological activities, such as antibacterial, anticoccidial, anti-inflammatory, antipsychotic, anticonvulsant, antifungal, antiviral, anticancer, etc. The introduction of a 2-Nitroalkyl moiety into the pyrrole nucleus has attracted much research interest. 2-(2-Nitroalkyl)pyrroles were demonstrated to be appealing intermediates for the synthesis of bioactive compounds [14] The introduction of a 2-Nitroalkyl moiety into the pyrrole nucleus has attracted much research interest. 2-(2-Nitroalkyl)pyrroles were demonstrated to be appealing intermediates for the synthesis of bioactive compounds [14]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
